One-pot synthesis of malononitriles by free radical reactions of ylidenemalononitrile with Et3B and iodoalkane in a water-ether biphase medium

Zhijay Tu, Chunchi Lin, Yaochung Jang, Yeong Jiunn Jang, Shengkai Ko, Hulin Fang, Ju Tsung Liu, Ching-Fa Yao

Research output: Contribution to journalArticle

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Abstract

The one-pot synthesis of malononitrile derivatives 4, 6, and 7 in moderate to high yields by the reaction of ylidenemalononitriles 3, prepared in situ from carbonyl compounds 1 and malononitrile 2 in the presence of ammonium acetate in aqueous solution at 50-60 °C, with Et3B or RI 5/Et3B in a water-diethyl ether biphase medium under an atmosphere of room temperature is reported. The reaction of Et3B with adamantyl iodides 8 and 10 under similar conditions gave 9 and 11 in high yields, respectively. However, low yields of the monoalkylated combined with dialkylated malonates 14 were obtained when benzaldehyde 1a was condensed with dimethylmalonate 12 followed by parallel free radical treatment in benzene solution.

Original languageEnglish
Pages (from-to)6133-6137
Number of pages5
JournalTetrahedron Letters
Volume47
Issue number34
DOIs
Publication statusPublished - 2006 Aug 21

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Free radical reactions
Ether
Free Radicals
Malonates
Carbonyl compounds
Water
Iodides
Benzene
Atmosphere
Derivatives
Temperature
dicyanmethane

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

One-pot synthesis of malononitriles by free radical reactions of ylidenemalononitrile with Et3B and iodoalkane in a water-ether biphase medium. / Tu, Zhijay; Lin, Chunchi; Jang, Yaochung; Jang, Yeong Jiunn; Ko, Shengkai; Fang, Hulin; Liu, Ju Tsung; Yao, Ching-Fa.

In: Tetrahedron Letters, Vol. 47, No. 34, 21.08.2006, p. 6133-6137.

Research output: Contribution to journalArticle

Tu, Zhijay ; Lin, Chunchi ; Jang, Yaochung ; Jang, Yeong Jiunn ; Ko, Shengkai ; Fang, Hulin ; Liu, Ju Tsung ; Yao, Ching-Fa. / One-pot synthesis of malononitriles by free radical reactions of ylidenemalononitrile with Et3B and iodoalkane in a water-ether biphase medium. In: Tetrahedron Letters. 2006 ; Vol. 47, No. 34. pp. 6133-6137.
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AU - Tu, Zhijay

AU - Lin, Chunchi

AU - Jang, Yaochung

AU - Jang, Yeong Jiunn

AU - Ko, Shengkai

AU - Fang, Hulin

AU - Liu, Ju Tsung

AU - Yao, Ching-Fa

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AB - The one-pot synthesis of malononitrile derivatives 4, 6, and 7 in moderate to high yields by the reaction of ylidenemalononitriles 3, prepared in situ from carbonyl compounds 1 and malononitrile 2 in the presence of ammonium acetate in aqueous solution at 50-60 °C, with Et3B or RI 5/Et3B in a water-diethyl ether biphase medium under an atmosphere of room temperature is reported. The reaction of Et3B with adamantyl iodides 8 and 10 under similar conditions gave 9 and 11 in high yields, respectively. However, low yields of the monoalkylated combined with dialkylated malonates 14 were obtained when benzaldehyde 1a was condensed with dimethylmalonate 12 followed by parallel free radical treatment in benzene solution.

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